The Berkshires Quintessential Picks

A guide to the classic and quintessential spots in the Berkshires.

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The Berkshires Quintessential Picks

A guide to the classic and quintessential spots in the Berkshires.

The Berkshires are made up of a chain of towns along the western border of Massachusetts. In the 19th century, it was the summer getaway for polite society with most of their mansions surrounding the Lenox area. Many of the mansions are gone, either burnt to the ground or have become hotels, but the genteel feeling of the area remains and it’s still a cultural center for music, dance and theater.

It’s also turning into a culinary destination. The distance from the farm to the table is short. Here it’s not a trend, it’s just the way they cook. This guide will help you find the more classic and quintessential places in the Berkshires for eating, drinking and food shopping. Check out our other FED | Guide for the newer spots.

CAFFEINE FIX

The Gallery at Shaker Dam Coffee | Photo Credit: Find. Eat. Drink.

Coffee & Photography | Shaker Dam Coffee

A small coffee house and gallery with photos taken by owner and photographer John Stanmeyer, who traveled the world as a photojournalist documenting war-torn areas for National Geographic. Located in a 1800s Shaker-style house in West Stockbridge, he’s more likely to chat with you about coffee brewing methods than f-stops. Get an iced coffee made with the in-house Japanese Oji water dripper that takes 8 hours to brew a cup.

Coffee | Lenox Coffee

Get your caffeine fix at this cafe owned by Berkshires native Gregg Charbonneau, who is the founder of Barrington Coffee Roasting Company in Lee.

“They source smaller farms and get different kinds of beans and they don’t over-roast.” - Chef Stephen Browning of Prairie Whale

52 Main Street, Lenox, MA 01240 | T: 413.637.1606

SHOPS

Charles Baldwin & Sons | Photo Credit: Find. Eat. Drink.

Vanilla Extract Makers | Charles Baldwin & Sons

Baldwin Extract | Photo Credit: Find. Eat. Drink.

The Baldwins have been making small batch vanilla extract for over a century. Made in their basement of a former carriage shop, they use imported Bourbon Vanilla Beans from Madagascar and 100-year-old barrels for aging. They sell their extract, as well as ice cream toppings, sugar blends and their signature Worcestershire sauce all made using their vanilla.

FARM STAND & MARKET

Farmers Market | Lenox Farmers Market

Located on the grounds of Shakespeare & Company, they sell local produce, poultry, cheeses, eggs, pies, cakes, hard ciders, sandwiches, pizzas and flowers.

“This market is on Fridays, which is good when you’re planning for a weekend. The Shakespeare and Company campus is beautiful during the day. There are a lot of people from the northern part of Columbia County and farmers from the Pittsfield area.” - Chef Scott Cole of Monterey General Store

Burgers | Lantern Bar & Grill

Vintage neon sign, TVs playing in the background and waitresses that call you “Hon.”

“They started the same year as the Oscars. It's been here for over 85 years. It completely goes against me in one way, but it agrees in another. It's a $5 burger served in this historic room and they've been doing it as it’s been done for decades and there is something that feels really cool about that.” - Chef Bjorn Somlo of Nudel

“They are about as local as it gets and they make a really great ciabatta.” - Chef Scott Cole of Monterey General Store

“They make a mean ciabatta and their chocolate sourdough bread (which has been the talk of the media nationwide) is perfect toasted with some butter. The are making by far the best bread in the area.” - Chef Brian Alberg of The Red Lion Inn

DINNER

New American | Mezze Bistro + Bar

Chef Nicholas Moulton creates a menu focusing on the Berkshires region and nose-to-tale philosophy. Owner and beverage director Nancy Thomas has co-authored a few cocktail books, so make sure to check out the bar list.

“It’s a great place for a really nice meal. They deliver a solid product and they do a great job with everything.” - Chef Bjorn Somolo of Nudel

American | John Andrews

Chef Dan Smith has won the respect of local chefs for his seasonal, fine dining restaurant in an old farm house.

“It's always been obvious to chef Dan Smith to take advantage of the local sustainable agriculture. It didn’t seem that obvious to everybody 20 years ago, but it did to him. He makes amazing dishes, like lamb from Lila Berle’s farm and seared duck breast. His fried oysters are extraordinarily delicious which, not local but amazing.” - Chef Scott Cole of Monterey General Store

“For chef Dan Smith's sweetbreads and farm-to-table loveliness. He’s got outdoor dining and a fireplace, so in any season it’s an even more special treat to dine here. And Eric knows his cocktails, too.” - Chef Daire Rooney of Allium Restaurant + Bar

FED24 To Go

FED24 To Go

Prep for your trip. Take the guide with you by downloading our FED24 To Go version.

Souvenirs

Souvenirs

Baldwin Vanilla

The Baldwins have been making small batch vanilla extract for over a century in West Stockbrige. They use imported Bourbon Vanilla Bean from Madagascar and 100-year-old barrels for aging. Stop into their former carriage house to pick up a bottle to bring home.

Cricket Creek Farm Cheese

One of the oldest, grass-based dairy farms in the region. Canyon Ranch chef Scott Uehlein is a fan. "Cricket Creek Farms embodies all that we love: cows are treated humanely (they are grass fed, roam on pastures, are not treated with hormones or antibiotics) and the cheese is made in an Old World style, which produces a far superior flavor and texture."